JPH0138779B2 - - Google Patents
Info
- Publication number
- JPH0138779B2 JPH0138779B2 JP55028201A JP2820180A JPH0138779B2 JP H0138779 B2 JPH0138779 B2 JP H0138779B2 JP 55028201 A JP55028201 A JP 55028201A JP 2820180 A JP2820180 A JP 2820180A JP H0138779 B2 JPH0138779 B2 JP H0138779B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- carried out
- selectivity
- aromatic
- amine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 150000004982 aromatic amines Chemical class 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- -1 aromatic alkyl amine Chemical class 0.000 claims 2
- 150000003973 alkyl amines Chemical class 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 150000005527 organic iodine compounds Chemical class 0.000 claims 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical group CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 4
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 4
- 239000002841 Lewis acid Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- CHHCCYVOJBBCIY-UHFFFAOYSA-N 3-chloro-n,n-dimethylaniline Chemical compound CN(C)C1=CC=CC(Cl)=C1 CHHCCYVOJBBCIY-UHFFFAOYSA-N 0.000 description 1
- WFGYSQDPURFIFL-UHFFFAOYSA-N 3-chloro-n-methylaniline Chemical compound CNC1=CC=CC(Cl)=C1 WFGYSQDPURFIFL-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 238000007126 N-alkylation reaction Methods 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- QCIFLGSATTWUQJ-UHFFFAOYSA-N n,4-dimethylaniline Chemical compound CNC1=CC=C(C)C=C1 QCIFLGSATTWUQJ-UHFFFAOYSA-N 0.000 description 1
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000003263 primary aromatic amine group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003336 secondary aromatic amines Chemical class 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
- C07C209/18—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT20800/79A IT1114212B (it) | 1979-03-07 | 1979-03-07 | Procedimento per la preparazione di alchil ammine aromatiche |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55127350A JPS55127350A (en) | 1980-10-02 |
| JPH0138779B2 true JPH0138779B2 (da) | 1989-08-16 |
Family
ID=11172243
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2820180A Granted JPS55127350A (en) | 1979-03-07 | 1980-03-07 | Manufacture of aromatic alkylamine |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4326079A (da) |
| JP (1) | JPS55127350A (da) |
| BE (1) | BE882135A (da) |
| DE (1) | DE3007196C2 (da) |
| DK (1) | DK156427C (da) |
| ES (1) | ES489718A0 (da) |
| FR (1) | FR2450807A1 (da) |
| GB (1) | GB2044261B (da) |
| IT (1) | IT1114212B (da) |
| NL (1) | NL179049C (da) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3136085A (en) * | 1962-03-12 | 1964-06-09 | Frank J Luketa | Suspension for trawl net panels and chafing gear |
| JPS6039666B2 (ja) * | 1982-09-23 | 1985-09-06 | ピ−ピ−ジ−・インダストリ−ズ・インコ−ポレ−テツド | Ｎ，ｎ−ビス（２，４，６−トリブロモフエニル）メチルアミン |
| FR2584720B1 (fr) * | 1985-07-11 | 1987-10-02 | Rhone Poulenc Sante | Procede de preparation de derives n-methyles de l'ergoline |
| DE4013471A1 (de) * | 1990-04-27 | 1991-10-31 | Fischer Ag Georg | Einrichtung zum stirnseitigen verschweissen von kunststoffteilen |
| WO2011024186A1 (en) | 2009-08-24 | 2011-03-03 | Keki Hormusji Gharda | Method for synthesis of n-alkyl carbazole and derivatives thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS49108028A (da) * | 1972-11-03 | 1974-10-14 | ||
| JPS52131534A (en) * | 1976-04-24 | 1977-11-04 | Basf Ag | Aralkylarylamine and preparation thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2187745A (en) * | 1934-09-01 | 1940-01-23 | Du Pont | Process for hydrogenating amides and imides to amines |
| US2944082A (en) * | 1957-12-20 | 1960-07-05 | Hercules Powder Co Ltd | Production of diethylmethylamine |
| NL130747C (da) * | 1961-07-21 | |||
| SU539031A1 (ru) * | 1975-06-12 | 1976-12-15 | Предприятие П/Я А-7850 | Способ получени -диэтил-мтолуидина |
-
1979
- 1979-03-07 IT IT20800/79A patent/IT1114212B/it active
-
1980
- 1980-02-22 US US06/123,918 patent/US4326079A/en not_active Expired - Lifetime
- 1980-02-26 GB GB8006479A patent/GB2044261B/en not_active Expired
- 1980-02-26 DE DE3007196A patent/DE3007196C2/de not_active Expired
- 1980-02-28 DK DK085580A patent/DK156427C/da not_active IP Right Cessation
- 1980-03-04 NL NLAANVRAGE8001302,A patent/NL179049C/xx not_active IP Right Cessation
- 1980-03-06 ES ES489718A patent/ES489718A0/es active Granted
- 1980-03-06 FR FR8005073A patent/FR2450807A1/fr active Granted
- 1980-03-07 BE BE0/199720A patent/BE882135A/fr not_active IP Right Cessation
- 1980-03-07 JP JP2820180A patent/JPS55127350A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS49108028A (da) * | 1972-11-03 | 1974-10-14 | ||
| JPS52131534A (en) * | 1976-04-24 | 1977-11-04 | Basf Ag | Aralkylarylamine and preparation thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| ES8103018A1 (es) | 1981-02-16 |
| ES489718A0 (es) | 1981-02-16 |
| DE3007196A1 (de) | 1980-09-11 |
| US4326079A (en) | 1982-04-20 |
| GB2044261B (en) | 1983-01-26 |
| FR2450807A1 (fr) | 1980-10-03 |
| NL179049C (nl) | 1986-07-01 |
| IT1114212B (it) | 1986-01-27 |
| NL179049B (nl) | 1986-02-03 |
| DK156427C (da) | 1990-01-22 |
| DK85580A (da) | 1980-09-08 |
| NL8001302A (nl) | 1980-09-09 |
| BE882135A (fr) | 1980-09-08 |
| IT7920800A0 (it) | 1979-03-07 |
| DE3007196C2 (de) | 1982-10-07 |
| FR2450807B1 (da) | 1984-12-14 |
| GB2044261A (en) | 1980-10-15 |
| DK156427B (da) | 1989-08-21 |
| JPS55127350A (en) | 1980-10-02 |
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